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Identification
YMDB IDYMDB01190
NamePC(18:1(9Z)/0:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionLysoPC(18:1(9Z)) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. Lysophosphatidylcholines can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) position. Fatty acids containing 16, 18 and 20 carbons are the most common. LysoPC(18:1(9Z)), in particular, consists of one chain of oleic acid at the C-1 position. Lysophosphatidylcholine is found in small amounts in most tissues. It is formed by hydrolysis of phosphatidylcholine by the enzyme phospholipase A2, as part of the de-acylation/re-acylation cycle that controls its overall molecular species composition. It can also be formed inadvertently during extraction of lipids from tissues if the phospholipase is activated by careless handling.
Structure
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Synonyms
  • 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine
  • 1-acyl-2-lyso-phosphatidylcholine
  • 1-Acyl-sn-glycero-3-phosphocholine
  • 1-acyl-sn-glycero-3-phosphocholines
  • 1-Acyl-sn-glycerol-3-phosphocholine
  • 1-Acylglycerophosphocholine
  • 1-oleoyl-glycero-3-phosphocholine
  • 1-Oleoyl-sn-glycero-3-phosphocholine
  • 1-Oleoylglycerophosphocholine
  • 2-Lysolecithin
  • 2-Lysophosphatidylcholine
  • 3-Oleoyl-rac-glycerol-1-phosphorylcholine
  • alpha-Acylglycerophosphocholine
  • Choline phosphate (ester) 3-ester with 1-monoolein
  • Choline phosphate 3-ester with 1-monoolein
  • GPCho(18:1(9Z)/0:0)[rac]
  • LPC
  • LPC(18:1)
  • LPC(18:1/0:0)
  • LPC(18:1n9/0:0)
  • LPC(18:1w9/0:0)
  • LyPC(18:1)
  • LyPC(18:1/0:0)
  • LyPC(18:1n9/0:0)
  • LyPC(18:1w9/0:0)
  • LysoPC(18:1)
  • LysoPC(18:1/0:0)
  • LysoPC(18:1n9/0:0)
  • LysoPC(18:1w9/0:0)
  • Lysophosphatidylcholine(18:1)
  • Lysophosphatidylcholine(18:1/0:0)
  • Lysophosphatidylcholine(18:1n9/0:0)
  • Lysophosphatidylcholine(18:1w9/0:0)
  • LysoPIC(18:1/0:0)
  • Olein-1-mono-3-phosphate ester with choline
  • Oleoyl lysolecithin
  • Oleoyl lysophosphatidylcholine
  • 1-Oleoyl-2-hydroxy-sn-glycero-3-phosphocholine
  • 1-Oleoyl-sn-glycero-3-phosphorylcholine
  • LPC 18:1
  • LPC 18:1(9Z)/0:0
  • LPC(18:1(9Z)/0:0)
  • LysoPC 18:1(9Z)/0:0
  • LysoPC(18:1(9Z)/0:0)
  • Lysophosphatidylcholine 18:1
  • Lysophosphatidylcholine(18:1(9Z)/0:0)
  • PC 18:1(9Z)/0:0
  • PC(18:1(9Z)/0:0)
  • 1-(9Z)-Octadecenoyl-sn-glycero-3-phosphocholine
  • LysoPC a C18:1
  • 1-(cis-9-Octadecenoyl)-sn-glycero-3-phosphocholine
  • 1-OGPC
  • 1-Oleoyl lysophosphatidylcholine
  • 1-Oleoyl-lysopc
  • 1-(9Z-Octadecenoyl)-glycero-3-phosphocholine
  • LysoPC(18:1(9Z))
CAS number3542-29-8
WeightAverage: 521.6673
Monoisotopic: 521.348139535
InChI KeyYAMUFBLWGFFICM-PTGWMXDISA-N
InChIInChI=1S/C26H52NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-26(29)32-23-25(28)24-34-35(30,31)33-22-21-27(2,3)4/h12-13,25,28H,5-11,14-24H2,1-4H3/b13-12-/t25-/m1/s1
IUPAC Name(2-{[(2R)-2-hydroxy-3-[(9Z)-octadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional IUPAC Name(2-{[(2R)-2-hydroxy-3-[(9Z)-octadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Chemical FormulaC26H52NO7P
SMILESCCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@]([H])(O)COP([O-])(=O)OCC[N+](C)(C)C
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-acyl-sn-glycero-3-phosphocholines. These are glycerophosphocholines in which the glycerol is esterified with a fatty acid at O-1 position, and linked at position 3 to a phosphocholine.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct Parent1-acyl-sn-glycero-3-phosphocholines
Alternative Parents
Substituents
  • 1-acyl-sn-glycero-3-phosphocholine
  • Phosphocholine
  • Fatty acid ester
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Alcohol
  • Organic oxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic salt
  • Amine
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.00028 g/LALOGPS
logP2.38ALOGPS
logP1.72ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area105.12 ŲChemAxon
Rotatable Bond Count25ChemAxon
Refractivity152.59 m³·mol⁻¹ChemAxon
Polarizability60.01 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB Pathways
Glycerophospholipid metabolismPW002493 ThumbThumb?image type=greyscaleThumb?image type=simple
Lysolipid incorporation into ER PC(18:1(9Z)/18:1(9Z))PW002788 ThumbThumb?image type=greyscaleThumb?image type=simple
Lysolipid incorporation into Mitochondria PC(18:1(9Z)/18:1(9Z))PW002796 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Glycerophospholipid metabolismec00564 Map00564
SMPDB Reactions
PC(18:1(9Z)/0:0) + waterGlycerophosphocholine + a carboxylate
PC(18:1(9Z)/0:0)PC(18:1(9Z)/18:1(9Z))
KEGG ReactionsNot Available
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
0.132 ± 0.0066 µM YEB media with 0.5 mM glucoseaerobicBrewer's yeastExperimentally Determined
Not Available
0.132 ± 0.0066 µM YEB media with 0.5 mM glucoseaerobicBrewer's yeastExperimentally Determined
Not Available
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • Ejsing, C. S., Sampaio, J. L., Surendranath, V., Duchoslav, E., Ekroos, K., Klemm, R. W., Simons, K., Shevchenko, A. (2009). "Global analysis of the yeast lipidome by quantitative shotgun mass spectrometry." Proc Natl Acad Sci U S A 106:2136-2141.19174513
Synthesis Reference:Chung, Guk Hoon; Kim, Sun Ki; Rhee, Joon Shick; Han, Jeong Joon. Process for preparing lysophospholipids using enzymes. U.S. (2001), 8 pp.
External Links:
ResourceLink
CHEBI ID17504
HMDB IDHMDB02815
Pubchem Compound ID5280634
Kegg IDC04230
ChemSpider ID17240641
FOODB IDFDB005287
Wikipedia IDNot Available
BioCyc IDPHOSPHATIDYLCHOLINE

Enzymes

General function:
Involved in metabolic process
Specific function:
Intracellular phospholipase B that catalyzes the double deacylation of phosphatidylcholine (PC) to glycerophosphocholine (GroPCho). Plays an important role in membrane lipid homeostasis. Responsible for the rapid PC turnover in response to inositol, elevated temperatures, or when choline is present in the growth medium
Gene Name:
NTE1
Uniprot ID:
Q04958
Molecular weight:
187131.0
Reactions
2-lysophosphatidylcholine + H(2)O → glycerophosphocholine + a carboxylate.